N,N-dimethyl-[1, 1'; 3', 1'']terphenyl-2'-ylmethyl-amine | 1429517-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-dimethyl-[1, 1'; 3', 1'']terphenyl-2'-ylmethyl-amine
• 英文别名: 2,6-diphenyl-N,N-dimethylbenzylamine；1-(2,6-diphenylphenyl)-N,N-dimethylmethanamine
• CAS: 1429517-70-3
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: NMBVLQMWAQYOCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-[1, 1'; 3', 1'']terphenyl-2'-ylmethyl-amine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到2,6-diphenyltoluene
  参考文献：
  名称：

  Cu(II)-Promoted Palladium-Catalyzed C–H Ortho-Arylation of N,N-Dimethylbenzylamines

  摘要：

  A novel protocol for palladium-catalyzed arylation of the C(sp(2))-H bond directed by a N,N-dimethylaminomethyl group in the presence of AgOAc and Cu(OAc)(2)center dot H2O is described. Various aryl iodides proved to be efficient coupling partners, furnishing the corresponding ortho monoarylated or diarylated arenes in Moderate to good yields. Cu(OAc)(2)center dot H2O is found to be the important additive to improve the yields in this transformation.

  DOI：

  10.1021/jo400186p
• 作为产物：
  描述：

  N,N-二甲基苄胺 、 碘苯 在 四(三苯基膦)钯 、 silver(I) acetate 、 copper(II) acetate monohydrate 、 溶剂黄146 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 60.5h， 以70%的产率得到N,N-dimethyl-[1, 1'; 3', 1'']terphenyl-2'-ylmethyl-amine
  参考文献：
  名称：

  Cu(II)-Promoted Palladium-Catalyzed C–H Ortho-Arylation of N,N-Dimethylbenzylamines

  摘要：

  A novel protocol for palladium-catalyzed arylation of the C(sp(2))-H bond directed by a N,N-dimethylaminomethyl group in the presence of AgOAc and Cu(OAc)(2)center dot H2O is described. Various aryl iodides proved to be efficient coupling partners, furnishing the corresponding ortho monoarylated or diarylated arenes in Moderate to good yields. Cu(OAc)(2)center dot H2O is found to be the important additive to improve the yields in this transformation.

  DOI：

  10.1021/jo400186p

文献信息

• Direct Oxidative Arylation of Aryl CH Bonds with Aryl Boronic Acids via Pd Catalysis Directed by the<i>N</i>,<i>N</i>-Dimethylaminomethyl Group
  作者：Ji-Cheng Zhang、Jiang-Ling Shi、Bi-Qin Wang、Ping Hu、Ke-Qing Zhao、Zhang-Jie Shi

  DOI：10.1002/asia.201403292

  日期：2015.4

  directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids with high efficiency and high regioselectivity under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho‐monoarylated or

  在芳烃条件下，钯，N，N-二甲基苄胺与芳基硼酸的邻位芳基化反应可直接构建联芳基骨架。的N，N-二甲基氨基甲基组在这样的氧化偶合首先应用于为定向基团。各种底物被证明是有效的偶联伙伴，在温和条件下以中等到良好的产率提供相应的邻-单芳基化或二芳基化的芳烃。
• Cu(II)-Promoted Palladium-Catalyzed C–H Ortho-Arylation of <i>N</i>,<i>N</i>-Dimethylbenzylamines
  作者：Ruokun Feng、Jinzhong Yao、Zunjun Liang、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1021/jo400186p

  日期：2013.4.19

  A novel protocol for palladium-catalyzed arylation of the C(sp(2))-H bond directed by a N,N-dimethylaminomethyl group in the presence of AgOAc and Cu(OAc)(2)center dot H2O is described. Various aryl iodides proved to be efficient coupling partners, furnishing the corresponding ortho monoarylated or diarylated arenes in Moderate to good yields. Cu(OAc)(2)center dot H2O is found to be the important additive to improve the yields in this transformation.